I like the idea but the execution would be really poor. We already have a lyceum intended for this thing, and I don't think anyone would bother having specific people as apprentices. Any guide crafted for this purpose would be too targeted and it'll confuse other n00bs who want to learn. Essentially you'd be reinventing the wheel every time with no real benefit.
A more real solution is writing general purpose guides in a standard format, some of which already exist in the form of "i am new to X". The format doesn't need to be fancy, just make your own or research stuff that works if you do feel fancy, and ensure everyone follows the same format.
I am no pedagogist, but if you intend to teach something from scratch, I think the best way is writing an introductory paragraph, maybe a small FAQ which mixes up with the rest of the article (sorta like predicting obvious questions and answering them neatly), and steadily teaching the basics of the thing you wanna cover.
You could go even further and make pro guides, to teach cool techniques and the like. It would take a lot of effort but if you guys can write a decent archive of articles intended for teaching the stuff you do here, you will not only educate existing n00bs, but potentially attract new ones.